Synthesis of Symmetrical Acetophenone Azine Derivatives as Colorimetric and Fluorescent Cyanide Chemosensors

Irmi, Nur Masyittah; Purwono, Bambang; Anwar, Chairil

doi:10.22146/ijc.64428

Cited by 6 publications

(5 citation statements)

References 22 publications

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“…Therefore, developing simple, efficient, and faster techniques is necessary. The color change can be used to detect anions using colorimetric chemosensors [9]. The methods provide a qualitative and quantitative analysis directly with the naked eye [10][11].…”

Section: ■ Introductionmentioning

confidence: 99%

Synthesis of Vanillin-Azine as Colorimetric Chemosensor of Sulfide Anion

Rokhmah

Mardjan²,

Purwono³

2022

Indones. J. Chem.

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Vanillin-azine (VA), (4,4'-((1E,1'E)-hydrazine-1,2-diylidenebis(methane-lylidene))bis(2-methoxyphenol) has been synthesized from vanillin and tested as anion colorimetric chemosensors for sulfide anion. The VA was obtained from a condensation reaction between vanillin and hydrazine hydrate with a mol ratio of 2:1 mol for 24 h at room temperature. The structure was elucidated using FTIR, GC-MS, 1H-NMR, and 13C-NMR spectrometers. The VA compound was examined as a colorimetric chemosensor for sulfide anion over several anions of CN−, F−, Cl−, Br−, I−, N3−, CH3COO−, and NO3−. The structure of the product showed agreement with all spectrometric data. The VA chemosensor tests indicated only selective to S2− anion followed by a color change from colorless to light blue in a DMF:HEPES buffer solution (DMF:HBS) medium (9:1, v/v, 10 mM, pH = 7.4). Filter paper strips can detect S2− anion with a color change from white to yellow. The VA chemosensor has a limit of detection (LOD) of 5.4 × 10−4 M, therefore, the VA chemosensor can be applied to detect S2− anion in tap water.

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Section: ■ Introductionmentioning

confidence: 99%

Synthesis of Vanillin-Azine as Colorimetric Chemosensor of Sulfide Anion

Rokhmah

Mardjan²,

Purwono³

2022

Indones. J. Chem.

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“…The simple condensation method was adopted to synthesize compound 2 ( Scheme 1 ) [ 38 , 39 , 40 , 41 ]. The mixture isolated compound 1 was separated from 2 by simply washing the obtained product with diethyl ether.…”

Section: Resultsmentioning

confidence: 99%

“…The reaction of 2,4-dihydroxy acetophenone with hydrazine hydrate in ethanol resulted in the formation of compound 2 with a 67% yield. The literature method [ 40 ] reported a yield of 68% for the un-crystallized final product. Hence, the synthesis method used for compound 2 here is comparable to the literature method considering the yield of 67% after crystallization.…”

Section: Resultsmentioning

confidence: 99%

Exploration of Molecular Structure, DFT Calculations, and Antioxidant Activity of a Hydrazone Derivative

et al. 2022

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The hydrazine derivatives are known to possess several biological activities including anticancer, antibacterial and anti-fungal, anticonvulsant, and antioxidant. This communication presents the synthesis, X-ray crystal structure analysis, DFT calculations, cell cytotoxicity, and antioxidant activity of the Schiff base 4,4′-((1E,1′E)-hydrazine-1,2-diylidenebis(ethan-1-yl-1-ylidene))bis(benzene-1,3-diol) (compound 2). We have also isolated the side product compound 1 and characterized it using single X-ray crystallography. The crystal structure of compound 1 depicts that the ensuing C‒H···N hydrogen bonding interaction is presented and discussed herein. In addition, the calculations using density functional theory (DFT) approximation supported by experimental 1H and 13C NMR studies on the key compound 2 are reported. The results of theoretical and experimental 1H and 13C NMR were concordant. The antioxidant activity of compound 2 was determined by using 2,2′-azinobis(3-ethylbenzthiazoline-6-sulfonic acid) (ABTS•+) radical cation assays and 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical assay. Compound 2 demonstrated excellent antioxidant activity in ABTS assay (IC50 = 4.30 ± 0.21 µM) and DPPH assay (IC50 = 81.06 ± 0.72 µM) with almost no cytotoxicity below 25 µM.

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“…In the agricultural field, azines exhibit herbicidal properties [ 11 , 12 ]. Azine-based polymers are successfully used for chemosensors [ 13 , 14 , 15 ] and they also possess promising cathodic abilities for organic batteries [ 16 , 17 , 18 ] and could be also employed for 2D field effect transistors in their crystallized phase as silicon [ 19 ]. Some azine-based polymers possess promising cathodic abilities for organic batteries and are vital in optoelectronic devices.…”

Section: Introductionmentioning

confidence: 99%

Selective Formation of Unsymmetric Multidentate Azine-Based Ligands in Nickel(II) Complexes

2022

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A mixture of 2-pyridine carboxaldehyde, 4-formylimidazole (or 2-methyl-4-formylimidazole), and NiCl2·6H2O in a molar ratio of 2:2:1 was reacted with two equivalents of hydrazine monohydrate in methanol, followed by the addition of aqueous NH4PF6 solution, afforded a NiII complex with two unsymmetric azine-based ligands, [Ni(HLH)2](PF6)2 (1) or [Ni(HLMe)2](PF6)2 (2), in a high yield, where HLH denotes 2-pyridylmethylidenehydrazono-(4-imidazolyl)methane and HLMe is its 2-methyl-4-imidazolyl derivative. The spectroscopic measurements and elemental analysis confirmed the phase purity of the bulk products, and the single-crystal X-ray analysis revealed the molecular and crystal structures of the NiII complexes bearing an unsymmetric HLH or HLMe azines in a tridentate κ3N, N’, N” coordination mode. The HLH complex with a methanol solvent, 1·MeOH, crystallizes in the orthorhombic non-centrosymmetric space group P212121 with Z = 4, affording conglomerate crystals, while the HLMe complex, 2·H2O·Et2O, crystallizes in the monoclinic and centrosymmetric space group P21/n with Z = 4. In the crystal of 2·H2O·Et2O, there is intermolecular hydrogen-bonding interaction between the imidazole N–H and the neighboring uncoordinated azine-N atom, forming a one-dimensional polymeric structure, but there is no obvious magnetic interaction among the intra- and interchain paramagnetic NiII ions.

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Synthesis of Symmetrical Acetophenone Azine Derivatives as Colorimetric and Fluorescent Cyanide Chemosensors

Cited by 6 publications

References 22 publications

Synthesis of Vanillin-Azine as Colorimetric Chemosensor of Sulfide Anion

Synthesis of Vanillin-Azine as Colorimetric Chemosensor of Sulfide Anion

Exploration of Molecular Structure, DFT Calculations, and Antioxidant Activity of a Hydrazone Derivative

Selective Formation of Unsymmetric Multidentate Azine-Based Ligands in Nickel(II) Complexes

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